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Unlocking Diverse Utility for π-Unsaturated Feedstocks: Development of Metal-Catalyzed Transfer Hydrogenative Methods and Concise Total Syntheses of Octalactins A and B
Unlocking Diverse Utility for π-Unsaturated Feedstocks: Development of Metal-Catalyzed Transfer Hydrogenative Methods and Concise Total Syntheses of Octalactins A and B
상세정보
- 자료유형
- 학위논문 서양
- 최종처리일시
- 20260311091516.5
- ISBN
- 9798270232740
- DDC
- 547
- 저자명
- Wu, Jessica
- 서명/저자
- Unlocking Diverse Utility for π-Unsaturated Feedstocks: Development of Metal-Catalyzed Transfer Hydrogenative Methods and Concise Total Syntheses of Octalactins A and B / Jessica Wu
- 발행사항
- [Sl] : The University of Texas at Austin, 2025
- 형태사항
- 1 electronic resource (739 pages)
- 주기사항
- Source: Dissertations Abstracts International, Volume: 87-06, Section: B.
- 주기사항
- Advisors: Krische, Michael J. Committee members: Hull, Kami L.; Que, Emily L.; Lee, Seongmin; Hsu, Ku-Lung Ken.
- 학위논문주기
- - Ph.D. : The University of Texas at Austin, 2025.
- 초록/해제
- 요약Carbonyl addition is a fundamental transformation in organic synthesis for creating new carbon-carbon bonds. Traditionally, this is executed through nucleophilic addition of a premetallated reagent to an electrophile such as an aldehyde. However, the organometallic nucleophiles utilized are pyrophoric, require multistep syntheses, and generate stoichiometric waste. Additionally, the electrophiles produced can often be unstable. To improve upon these disadvantages, a suite of novel transition metal-catalyzed methods to form carbon-carbon bonds via hydrogen auto-transfer have been developed and will be described herein. Transfer hydrogenative processes can engage abundant feedstocks, such as butadiene, as pronucleophiles and directly employ primary alcohols as proelectrophiles circumventing the need for stoichiometric organometallic reagents and direct formation of intractable aldehydes.The methods discussed in this dissertation will include 1) ruthenium-catalyzed coupling of β-hydroxy esters with butadiene, 2) ruthenium-iodide-JOSIPHOS catalyzed anti-crotylation of primary alcohols mediated by methyl allene and butadiene, 3) rhodium-catalyzed transfer hydrogenation-redox isomerization of primary alcohols with butadiene to synthesize ketones, and 4) ruthenium-catalyzed dearomative addition-hydrogen auto-transfer alkylation of N-heteroarenes by dienes. Furthermore, the ruthenium-catalyzed functionalization of β-hydroxy esters methodology was applied to the concise total syntheses of octalactins A and B, furnishing these natural products in 11 and 10 steps longest linear sequence, respectively. The synthetic route achieved within this body of work is the shortest of all reported syntheses.
- 언어주기
- English
- 일반주제명
- Chemistry
- 일반주제명
- Analytical chemistry
- 일반주제명
- Organic chemistry
- 키워드
- Feedstocks
- 키워드
- Octalactins
- 기타저자
- The University of Texas at Austin Chemistry
- 기본자료저록
- Dissertations Abstracts International. 87-06B.
- 전자적 위치 및 접속
- 로그인 후 원문을 볼 수 있습니다.
MARC
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■007cr|nu||||||||
■020 ▼a9798270232740
■040 ▼aMiAaPQD▼beng▼cMiAaPQD▼erda
■082 ▼a547
■1001 ▼aWu, Jessica▼eauthor.
■24510▼aUnlocking Diverse Utility for π-Unsaturated Feedstocks: Development of Metal-Catalyzed Transfer Hydrogenative Methods and Concise Total Syntheses of Octalactins A and B ▼cJessica Wu
■260 ▼a[Sl]▼bThe University of Texas at Austin▼c2025
■264 1▼aAnn Arbor▼bProQuest Dissertations & Theses▼c2025
■300 ▼a1 electronic resource (739 pages)
■336 ▼atext▼btxt▼2rdacontent
■337 ▼acomputer▼bc▼2rdamedia
■338 ▼aonline resource▼bcr▼2rdacarrier
■500 ▼aSource: Dissertations Abstracts International, Volume: 87-06, Section: B.
■500 ▼aAdvisors: Krische, Michael J. Committee members: Hull, Kami L.; Que, Emily L.; Lee, Seongmin; Hsu, Ku-Lung Ken.
■5021 ▼bPh.D.▼cThe University of Texas at Austin▼d2025.
■520 ▼aCarbonyl addition is a fundamental transformation in organic synthesis for creating new carbon-carbon bonds. Traditionally, this is executed through nucleophilic addition of a premetallated reagent to an electrophile such as an aldehyde. However, the organometallic nucleophiles utilized are pyrophoric, require multistep syntheses, and generate stoichiometric waste. Additionally, the electrophiles produced can often be unstable. To improve upon these disadvantages, a suite of novel transition metal-catalyzed methods to form carbon-carbon bonds via hydrogen auto-transfer have been developed and will be described herein. Transfer hydrogenative processes can engage abundant feedstocks, such as butadiene, as pronucleophiles and directly employ primary alcohols as proelectrophiles circumventing the need for stoichiometric organometallic reagents and direct formation of intractable aldehydes.The methods discussed in this dissertation will include 1) ruthenium-catalyzed coupling of β-hydroxy esters with butadiene, 2) ruthenium-iodide-JOSIPHOS catalyzed anti-crotylation of primary alcohols mediated by methyl allene and butadiene, 3) rhodium-catalyzed transfer hydrogenation-redox isomerization of primary alcohols with butadiene to synthesize ketones, and 4) ruthenium-catalyzed dearomative addition-hydrogen auto-transfer alkylation of N-heteroarenes by dienes. Furthermore, the ruthenium-catalyzed functionalization of β-hydroxy esters methodology was applied to the concise total syntheses of octalactins A and B, furnishing these natural products in 11 and 10 steps longest linear sequence, respectively. The synthetic route achieved within this body of work is the shortest of all reported syntheses.
■546 ▼aEnglish
■590 ▼aSchool code: 0227
■650 4▼aChemistry
■650 4▼aAnalytical chemistry
■650 4▼aOrganic chemistry
■653 ▼aFeedstocks
■653 ▼aOrganometallic nucleophiles
■653 ▼aHydrogenative methods
■653 ▼aConcise total syntheses
■653 ▼aOctalactins
■7102 ▼aThe University of Texas at Austin▼bChemistry.▼edegree granting institution.
■7201 ▼aKrische, Michael J.▼edegree supervisor.
■7730 ▼tDissertations Abstracts International▼g87-06B.
■85640▼uhttp://www.riss.kr/pdu/ddodLink.do?id=T17361248▼nKERIS▼z이 자료의 원문은 한국교육학술정보원에서 제공합니다.
